Tetrafluoroboric acid → HCID 21270916, compound

HRID 1193944Notes

Reaction equation

HRID 1193944 reaction equation
N[C:2]1[CH:3]=[C:4]([C:13]2[N:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][N:14]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[F:25][B-](F)(F)F.[H+].N([O-])=O.[Na+]>O1CCOCC1.O>[F:25][C:2]1[CH:3]=[C:4]([C:13]2[N:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][N:14]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 21270980HCID 21270980, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21270916HCID 21270916, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

56 g of 2-(3-amino-4-n-pentylphenyl)-5-n-hexylpyrimidine (m.p. 92°, obtainable by reaction of 2-(4-n-pentylphenyl)-5-n-hexylpyrimidine (c.p. 28.5°) with nitric acid to give 2-(3-nitro-4-n-pentylphenyl)-5-n-hexylpyrimidine (m.p. 41.5°) and hydrogenation on Raney nickel) is dissolved in 150 ml of dioxane at 50° and 208 ml of 35% tetrafluoroboric acid are added dropwise, with stirring. After one hour, the resulting emulsion is cooled to 0°, whereupon crystallization occurs. A solution of 20 g of sodium nitrite in 150 ml of water is added to the suspension and the mixture is stirred for one hour. The resulting mixture diazonium tetrafluoborate is filtered off with suction, washed with ice-water and dried. 5 g of the diazonium salt is heated at 200° until the evolution of gas has ended. 2-(3-Fluoro-4-n-pentylphenyl)-5-n-hexylpyrimidine of m.p. 30° is obtained by purification by chromatography.

Workup

  1. temperaturethe resulting emulsion is cooled to 0°, whereupon crystallization
  2. stirringthe mixture is stirred for one hour
  3. filtrationThe resulting mixture diazonium tetrafluoborate is filtered off with suction
  4. washwashed with ice-water
  5. customdried
  6. temperature5 g of the diazonium salt is heated at 200° until the evolution of gas

Sources & evidence

ORD record
ord-15e4a83e2e7c4ed9bfa3ae8c52b54203
Source dataset
uspto-grants-1989_03
Patent number
US04812258

Reaction notes

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